YHM - ORD

C$ 194 Find Cheap Flights from Hamilton to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hamilton to Chicago departing on 23/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hamilton to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hamilton to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 554
WestJet
Fri 22/5Tue 26/5
YHM - ORD • 1 stop
Cheapest one-way flights
C$ 194
Air Canada
Tue 23/6
YHM - ORD • 1 stop
Direct flights
Not available
There are currently no direct flights between Hamilton and Chicago. You’ll need at least 1 connection.
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hamilton to Chicago (YHM-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hamilton to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hamilton to Chicago

Fri, 22 May - Tue, 26 May
WestJet Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
WestJet Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 554WestJet
Sat, 16 May - Mon, 18 May
Multiple Airlines Logo
8:15 a.m. - 11:15 p.m.
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 591Multiple Airlines
Sat, 13 Jun - Sat, 20 Jun
Multiple Airlines Logo
8:15 a.m. - 11:15 p.m.
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:10 a.m. - 3:55 p.m.
ORD
-
YHM
9h 45m
1 stop
C$ 602Multiple Airlines
Fri, 22 May - Sun, 24 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:14 p.m.
ORD
-
YHM
27h 44m
2 stops
C$ 604Multiple Airlines
Fri, 22 May - Sun, 24 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:14 p.m.
ORD
-
YHM
27h 44m
2 stops
C$ 623Multiple Airlines
Sat, 23 May - Sat, 30 May
Multiple Airlines Logo
8:15 a.m. - 11:15 p.m.
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 625Multiple Airlines
Fri, 22 May - Sun, 24 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:14 p.m.
ORD
-
YHM
27h 44m
2 stops
C$ 629Multiple Airlines
Fri, 22 May - Sun, 24 May
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 10:14 p.m.
ORD
-
YHM
27h 44m
2 stops
C$ 630Multiple Airlines
Sat, 30 May - Sat, 6 Jun
Multiple Airlines Logo
8:15 a.m. - 11:15 p.m.
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 631Multiple Airlines
Sat, 13 Jun - Sat, 20 Jun
Multiple Airlines Logo
8:15 a.m. - 11:15 p.m.
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:10 a.m. - 3:55 p.m.
ORD
-
YHM
9h 45m
1 stop
C$ 637Multiple Airlines
Booking Insights

Good to know

Cheapest flightC$ 194
Flight from Hamilton to Chicago

When to book flights from Hamilton to Chicago

Are your dates flexible? Find out the best times to travel from Hamilton to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hamilton to Chicago flights

  • What is the cheapest flight from Hamilton to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Hamilton to Chicago O'Hare Intl Airport was C$ 194 for a one-way ticket and C$ 554 for a round-trip.

  • Which airports will I be using when flying from Hamilton to Chicago?

    Hamilton airport is called Hamilton and the only airport in Chicago is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Hamilton to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Hamilton to Chicago?

    Star Alliance is the only airline alliance operating flights between Hamilton and Chicago.

  • How does KAYAK find such low prices on flights from Hamilton to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hamilton to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hamilton to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hamilton is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hamilton to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hamilton with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hamilton to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hamilton up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Hamilton to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Hamilton to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hamilton to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 10983 reviews
7.1Comfort
7.8Crew
7.3Boarding
6.3Food
6.8Entertainment
Airline reviews

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

10.0 ExcellentAnonymous, Apr 2026
YYZ - EWR
Read more Air Canada reviews

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Everything you need to know for your flight from Hamilton to Chicago

Information on your arrival and departure airports

Hamilton (YHM)
O'Hare Intl (ORD)